Lindsey's Story Pt 1

Lindsey becomes curious about sex with two men and double penetration.

Please note that my stories are often the result of my very active and vivid imagination. Portions of some stories are taken from my life experiences, but I am not telling what parts those may be. I may or may not be an actual character in my stories, and they may or may not be something I would choose to do.

Lindsey had recently gotten divorced. Her husband had been mentally and physically abusive and in the last several years of the marriage, things had gotten even worse. She and her husband slept in separate bedrooms and barely even talked anymore, let alone touch. She later found out he had had several affairs. After such a long time without sex, she went a little crazy, just looking for anything with a cock to fuck. Lindsey had also recently started a new job and there was a group of girls who went out every Friday night. She was soon invited to join them one Friday and quickly became a regular with them.

They frequented several local clubs and knew many of the other regular patrons. After a while, some of the men became friendlier with her, and she began flirting with them. She hooked up with a few of them and went out on a couple of dates, but nothing came of any of them. That was ok with Lindsey, as she really was not looking for anything serious right now. She had married young and had not really dated much before she met her husband to be. So at this time, she was kind of looking to “sow some wild oats”.

As girls will do sometimes when they get together, they got to talking about men and their fantasies about them. They talked about how men often exaggerated the size of their cocks, their lasting power, and just their prowess with women in general. They all got laughs about these discussions since they found them to rarely be completely true. There was the occasional truth shared about the one guy who’s cock was almost too big to take and the one who had an amazing tongue (enough said). And one of the girls told of the time she spent naked with this one guy for an entire weekend. She said he made her cum sooo many times, she had lost count. He had had a nice size cock, and was very skilled in using it, along with his tongue and fingers.

Lindsey joked around with the others putting in her share of stories about her experiences. But her husband had been a poor lover who had only rarely given her orgasms. He did not want to have children and refused to use a condom. Although she had been on birth control pills, he did not believe her, and so pulled out before he came. Then Lindsey either sucked him off or gave him a hand job. Since he really never concerned himself much with Lindsey’s needs, she usually went into the bathroom afterwards and masturbated. Due to this, she tried to make up some stories so she would fit in with the others.

Over the first few months after her divorce, she had slept with about a dozen different guys, mostly just one night stands with men she barely knew. She kind of settled down after she started going out with her new friends from work, though she also did sleep with a few of the guys she dated from the bar. Also, at this time, Lindsey wanted a child badly and did not care if she got pregnant, so she would have unprotected sex with any guy she could find. And she discovered that most men were very easy to seduce. If she had gotten pregnant, she would have been overjoyed and would have raised the baby on her own.

One night while she was out with the other girls, she saw these two guys talking to a girl at the other end of the bar. One was sitting next to her and the other was standing behind her. They were both very close to her, touching her shoulder or her arm and whispering in her ear. She was obviously enjoying the attention, flirting back, leaning into the guy behind her and twirling her hair as she talked and laughed with them. The man sitting next to her began rubbing her back and slowly worked his hand inside the back of her blouse. She tilted her head towards the guy standing behind her and began kissing him. Then one of them whispered something to her, they finished their drinks and left the bar together.

Lindsey watched this interaction with a great deal of interest. She felt a pang of jealousy at the same time felt a twitching in her pussy. She began to wonder what being with two guys would be like and just what would happen. She remembered one time when her husband had made her watch a porn film. In it were a number of scenes where several guys took turns fucking one girl. At one point, two of the guys had both their cocks in her pussy. Lindsey doubted that she could ever do that. There was another scene where the girl was riding one of the cocks and a second guy came up behind her and pushed his cock into her ass.

Lindsey was not totally naïve, but she had never had anal sex and could not imagine how it felt. She only remembered that it looked rather painful as the girl in the movie winced when she was penetrated and as she was being fucked. Her husband had suggested it to her once, but she had refused him and he never asked again. But watching the two guys in the bar and imagining what they might have done really got her to thinking about what it would be like to have two men as sexual partners at the same time.

Shortly after moving out of her home when she divorced, a friend had given her a vibrator as a joke. It had several covers that went over the head of the vibrator. One was a long, relatively thin cover that looked like a long finger. When she got home that night, she pulled out the vibrator and some KY. She took off her clothes and laid down on her side on her bed. She reached around and put some of the lube around her hole and more on the cover. She turned on the vibrator and put the tip of the cover against her hole. She tried pushing it in but felt herself tensing against it. It was also a bit painful.

Lindsey tried to relax her muscles and push it in her again. This time she was able to get it in an inch or so before she felt herself push and expel the vibrator. She waited a minute, added a little more lube around her ass, trying to work it in a bit with her finger. She took a few deep breaths then relaxed and tried again. This time, she felt the vibrator go all the way in, popping a bit as it got past the inner muscles. She just left it there, not moving it and just feeling the vibes. After a minute, she started slowly moving it in and out. Lindsey was surprised when after about five or six minutes, she felt that familiar wave over come her and she had an orgasm. But it was just a little different than those she had had in the past.

Her curiosity piqued, Lindsey got up the courage to go to an adult book store and find a couple of other toys, which she paid for with cash and brought home. One of the toys was a small butt plug. The widest part was about half again as wide as the finger cover she had used on herself already. The other was a rubber replica of a cock. It was flesh colored and shaped just like a cock, complete with balls. It had a suction cup on the bottom of it so it could be attached to a flat surface like a chair and she could climb on and ride it. It was soft, yet firm, and had veins and texture to look and feel like skin. The store had bigger dildos, but she felt some of them were just too large. The one she selected was just a bit larger in size then any of the men she had been with.

When she got home, she could barely wait to try everything out. Lindsey experimented with several surfaces to see which worked best with the suction cup on the dildo. She decided it needed to be something she could straddle easily, so she could move up and down. She found that using the corner of one of the wooden chairs to her dining room table gave her sufficient room to move around. Also, she could face the back of the chair and use it to help her move up and down on the dildo. Once she had everything in place, Lindsey stripped naked and lubed up the butt plug. It took a bit of doing, but she finally got it inside her ass. It was a bit uncomfortable at first, so she just decided to let it sit there.

Next, she applied a liberal amount of the KY to the entire length of the dildo. She straddled the chair and tried to lower herself onto it. She was having some trouble as she expected she might, and added a bit more lube to the dildo and her pussy, but still was unable to get it in very far. Finally, she began to play with her clit and was getting aroused. While still playing with herself, she tried lowering herself on to the dildo again. This time she was successful in lowering herself all the way down.

She slowly began moving up and down on the cock. It was really stretching her pussy, but it felt very good. Each time she lowered herself, she could feel the additional pressure caused by the butt plug. The sensation was like nothing she had ever felt before. Lindsey was beginning to think she might actually like to have two guys in her at the same time. Now she was going to have to figure out just how to make that happen.

Next time Lindsey was out with her girl friends, she turned the subject to fantasies and asked if any of the others had the same fantasy or had actually been with two men and been double penetrated. Several admitted they did have that fantasy, but none of them had ever done it for real. The next weekend, they were planning on a longer girl’s night out rather than the few drinks they had when they went out on after work. She arrived at the bar early and saw the girl from before sitting alone. Lindsey walked over and sat down at the empty stool next to her.

”Hi, I’m Lindsey” she said, extending her hand.

“Alexis” the girl replied.

“Are you here alone? I am meeting some friends and you are welcome to join us if you like.”

“I would like that. I’m kind of new in town and really don’t know that many people here. I live within walking distance, so this is a handy place to come for a drink or two after work.”

When Lindsey’s friends began to arrive, she introduced Alexis to each one of them. They all greeted her and welcomed her into the group. Lindsey paid her particular attention. In the back of her mind, she wanted to get to know Alexis better. She wanted to ask her about the two men. What was it like? Had she done that type of thing often? And now that she knew that Alexis was new to the area, how did she make that connection with the two guys? Now that Lindsey had experienced the feeling of having something in her ass, and having both her ass and pussy filled at the same time, she was very fascinated in having it happen. At the same time, she was a bit apprehensive about doing it for real. Talking to someone who had actually done it might belay her fears.

When the time came to leave, Lindsey offered to drive Alexis home, even though it was only a few blocks. At first Alexis protested that it was unnecessary, but Lindsey insisted and she finally gave in. Lindsey said goodbye to her friends and the two girls walked out to her car. When they arrived at Alexis’s, she invited Lindsey to come in for a drink. They sat and chatted for a bit and finally Lindsey got up the courage to ask the question that had been on her mind all night.

“Do you mind if I ask you a question? It’s rather personal, so if you don’t want to answer, I’ll certainly understand.”

“Sure, ask away and I will answer if I can.”

“Last week, I saw you with those two guys. They seemed to be getting rather intimate with you, and then the three of you left. Though I can’t be certain of course, I have to assume that something sexual happened. So I guess my first question would be whether or not that assumption is correct. And before you answer, let me tell you the reason I am asking. I have recently become very curious about being with two men. None of my friends have and I am just wondering what it would be like. Also, please don’t get the idea that the only reason I talked to you tonight was to ask you about this. While it is part of the reason, I mainly introduced myself because you were sitting there alone, and I know how that is.”

“Well, I do thank you for coming over and talking to me. I have been going to that bar at least once a week now for the last month, and so far, other than those two guys, the only person that has spoken to me is the bartender. And to answer your question, yes your assumption is correct.”

“OK. Well that leads me to a whole bunch of other questions, if you don’t mind talking about it. And feel free to stop me at any point or refuse to answer any particular question. They are all rather personal and we have just met.”

“I don’t mind and will try to answer your questions if I can.”

“Was that the first time you have been with two men at the same time?”

“No. I enjoy men and have been with multiple men a number of times.”

“Wow! So you have actually been with more than two men at once?”

“Yes. I have been with three guys four or five times, and once was with four men.”

“OK. So then I guess my next question is what do you do with them? By that I mean, do they take turns or do you take two at the same time? I know that is a pretty personal question, but I am really curious to know what it would be like to be penetrated by two men at once. I have never had anal sex and until recently, never had anything in my ass. I was not even sure I would like it, but I tried with some toys, and found it to be kind of pleasurable.”

“Well, I will tell you the answer to your question is yes. I have been double penetrated, and with a third man, also sucked one off at the same time. It is a truly amazing experience. The feeling of fullness and of having every inch of my ass and pussy being stimulated at the same time more than doubles the pleasure of the sexual encounter. Throw in the fact that two sets of hands are doing things to other parts of my body and it is hard to describe the feeling. And toys just can’t compare to the feeing of a live hard cock inside you. I would definitely recommend trying it at least once.”

“May I ask you how it was the first time you tried it? When I tried a toy in my ass the first time, I had a bit of trouble getting it in, and it was quite thin. Then I went out and bought a smallish butt plug, though it was bigger than the dildo, and that kind of hurt when I first put it in. I noticed a little blood as well while I was cleaning up afterwards.”

“Yes, the first time can be a little uncomfortable. Using toys or your fingers to stretch yourself out a bit will help. It also helps you to learn how to relax your muscles as you are being penetrated. And of course, sufficient lubrication is a definite must. It makes everything slip in so much easier. If you are planning on hooking up and think you will be somewhere other than your home, carry a bottle of KY in your purse.”

“Really?? Well then I guess my last question is how do you find two guys willing to do that? I would think that not all guys would want to be naked with another naked guy right there, let alone have their cocks in such close proximity to each other.”

“Honey, it’s easier than you might think. Yes, some guys are very homophobic, and while they might take turns with a girl, would not have sex at the same time. But sometimes two buddies are just as willing to pick up and have sex with one girl as they are to find two girls willing to go and have sex. And more often than you may think, the two couples will have sex in close proximity. Like they will go back to one person’s place, or rent a single motel room with two beds. And quite often, it will turn into a group sex thing where everyone shares everything with everybody, and I mean everything.”

“Holy shit!!”

Alexis laughed loudly at that and Lindsey joined in. Lindsey thanked her for being so open and honest in her answers, then said it was late, she should really get going. Alexis said that if she ever had anymore questions, she would be glad to try and answer them. They walked to the door, and Alexis leaned over and gave Lindsey a hard passionate kiss.

“Anytime you would like to pursue that kiss further, just let me know.”

Lindsey’s head was reeling as she left and drove home. The kiss had stirred something in her that she had never suspected. She was not sure if it was just the unexpectedness of it or if there was something else. But this evening had certainly given her a lot to think about.

To be continued……

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